U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H14N3O6P
Molecular Weight 279.1874
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIDOFOVIR ANHYDROUS

SMILES

c1cn(C[C@@]([H])(CO)OCP(=O)(O)O)c(nc1=N)O

InChI

InChIKey=VWFCHDSQECPREK-LURJTMIESA-N
InChI=1S/C8H14N3O6P/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16)/t6-/m0/s1

HIDE SMILES / InChI

Molecular Formula C8H14N3O6P
Molecular Weight 279.1874
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10473024 | https://www.ncbi.nlm.nih.gov/pubmed/8630098

Cidofovir is an antiviral nucleotide analogue with significant activity against cytomegalovirus (CMV) and other herpesviruses. Cidofovir suppresses cytomegalovirus (CMV) replication by selective inhibition of viral DNA synthesis. Biochemical data support selective inhibition of CMV DNA polymerase by cidofovir diphosphate, the active intracellular metabolite of cidofovir. Incorporation of cidofovir into the growing viral DNA chain results in reductions in the rate of viral DNA synthesis. Cidofovir is indicated for the treatment of CMV retinitis in patients with acquired immunodeficiency syndrome.

CNS Activity

Curator's Comment:: In rabbits, radiolabelled cidofovir crossed the blood brain barrier but were found at much lower levels than were observed in the kidney tissue. In rats i.v. administered cidofovir does not seem to cross the blood-brain barrier efficiently. No human data available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VISTIDE

Approved Use

Cidofovir injection is indicated for the treatment of cytomegalovirus retinitis in patients with acquired immunodeficiency syndrome (AIDS).

Launch Date

8.3574718E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.34 μg/mL
3 mg/kg 1 times / week other, intravenous
dose: 3 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
11.5 μg/mL
5 mg/kg 1 times / week other, intravenous
dose: 5 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.12 μg/mL
1 mg/kg 1 times / week other, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
19.96 μg × h/mL
3 mg/kg 1 times / week other, intravenous
dose: 3 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
28.34 μg × h/mL
5 mg/kg 1 times / week other, intravenous
dose: 5 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
8.35 μg × h/mL
1 mg/kg 1 times / week other, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.72 h
3 mg/kg 1 times / week other, intravenous
dose: 3 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.42 h
5 mg/kg 1 times / week other, intravenous
dose: 5 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.44 h
1 mg/kg 1 times / week other, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5 % single, topical
Highest studied dose
Dose: 5 %
Route: topical
Route: single
Dose: 5 %
Sources: Page: p.2998
unhealthy, 21–66
n = 96
Health Status: unhealthy
Condition: Recurrent genital herpes
Age Group: 21–66
Sex: M+F
Population Size: 96
Sources: Page: p.2998
Disc. AE: Ulceration...
AEs leading to
discontinuation/dose reduction:
Ulceration (2%)
Sources: Page: p.2998
10 mg/kg single, intravenous
Highest studied dose
Dose: 10 mg/kg
Route: intravenous
Route: single
Dose: 10 mg/kg
Sources: Page: p.154
unhealthy
n = 5
Health Status: unhealthy
Condition: Acquired immunodeficiency syndrome (AIDS)
Sex: M+F
Population Size: 5
Sources: Page: p.154
10 mg/kg single, oral
Highest studied dose
Dose: 10 mg/kg
Route: oral
Route: single
Dose: 10 mg/kg
Sources: Page: p.154
unhealthy
n = 5
Health Status: unhealthy
Condition: Acquired immunodeficiency syndrome (AIDS)
Sex: M+F
Population Size: 5
Sources: Page: p.154
5 mg/kg 1 times / week multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / week
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Sources: Page: p.1
Disc. AE: Acute renal failure...
Other AEs: Renal impairment, Neutropenia...
AEs leading to
discontinuation/dose reduction:
Acute renal failure
Other AEs:
Renal impairment
Neutropenia
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Ulceration 2%
Disc. AE
5 % single, topical
Highest studied dose
Dose: 5 %
Route: topical
Route: single
Dose: 5 %
Sources: Page: p.2998
unhealthy, 21–66
n = 96
Health Status: unhealthy
Condition: Recurrent genital herpes
Age Group: 21–66
Sex: M+F
Population Size: 96
Sources: Page: p.2998
Neutropenia
5 mg/kg 1 times / week multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / week
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Sources: Page: p.1
Renal impairment
5 mg/kg 1 times / week multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / week
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Sources: Page: p.1
Acute renal failure Disc. AE
5 mg/kg 1 times / week multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / week
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Sources: Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
yes
yes
PubMed

PubMed

TitleDatePubMed
Induction of apoptosis by cidofovir in human papillomavirus (HPV)-positive cells.
2000
Predictive efficacy of SCID-hu mouse models for treatment of human cytomegalovirus infections.
2001
Successful treatment of severe respiratory papillomatosis with intravenous cidofovir and interferon alpha-2b.
2001 Apr
Cidofovir added to highly active antiretroviral therapy in AIDS-associated progressive multifocal leukoencephalopathy.
2001 Apr 13
Human renal organic anion transporter 1 (hOAT1) and its role in the nephrotoxicity of antiviral nucleotide analogs.
2001 Apr-Jul
An efficient process for the synthesis of cyclic HPMPC.
2001 Apr-Jul
Cytomegalovirus treatment options in immunocompromised patients.
2001 Aug
Infections after stem cell transplantation in children: state of the art and recommendations.
2001 Aug
Potent anti-retroviral therapy with or without cidofovir for AIDS-associated progressive multifocal leukoencephalopathy: extended follow-up of an observational study.
2001 Aug
A case of human orf in an immunocompromised patient treated successfully with cidofovir cream.
2001 Aug
Antiviral drugs: current state of the art.
2001 Aug
Acute renal failure in a lung transplant patient after therapy with cidofovir.
2001 Dec
Novel non-nucleoside inhibitors of cytomegaloviruses (BAY 38-4766): in vitro and in vivo antiviral activity and mechanism of action.
2001 Dec
Antiviral activity of NMSO3 against adenovirus in vitro.
2001 Dec
Antiviral prophylaxis with twice daily topical cidofovir protects against challenge in the adenovirus type 5/New Zealand rabbit ocular model.
2001 Dec
Long-term remission of Kaposi sarcoma-associated herpesvirus-related multicentric Castleman disease with anti-CD20 monoclonal antibody therapy.
2001 Dec 1
Reversal of CSF positivity for JC virus genome by cidofovir in a patient with systemic lupus erythematosus and progressive multifocal leukoencephalopathy.
2001 Feb
The antiviral resistance and replication of cidofovir-resistant adenovirus variants in the New Zealand White rabbit ocular model.
2001 Jul
Efficacy and tolerability of topical 1% cidofovir cream for the treatment of external anogenital warts in HIV-infected persons.
2001 Jun
[Efficacy of cidofovir in an HIV infected patient with an acyclovir and foscarnet resistant herpes simplex virus infection].
2001 Jun-Jul
[Oncogenic human papillomaviruses in extra-genital Bowen disease revealed by in situ hybridization].
2001 Jun-Jul
Cidofovir.
2001 Mar
[Anterior uveitis and cidofovir].
2001 May
Successful treatment of aids related PML with HAART and cidofovir.
2001 May 29
Clinical applications of a novel sustained-release injectable drug delivery system: DepoFoam technology.
2001 May-Jun
Cidofovir as primary pre-emptive therapy for post-transplant cytomegalovirus infections.
2001 Nov
Successful treatment of foscarnet-resistant herpes simplex stomatitis with intravenous cidofovir in a child.
2001 Nov
Cidofovir treatment of progressive multifocal leukoencephalopathy in a patient receiving highly active antiretroviral therapy.
2001 Nov
Selection of the same mutation in the U69 protein kinase gene of human herpesvirus-6 after prolonged exposure to ganciclovir in vitro and in vivo.
2001 Nov
Nucleoside phosphonate interactions with multiple organic anion transporters in renal proximal tubule.
2001 Nov
Prevention and inhibition of nasopharyngeal carcinoma growth by antiviral phosphonated nucleoside analogs.
2001 Nov 1
Cytomegalovirus ventriculoencephalitis in a bone marrow transplant recipient receiving antiviral maintenance: clinical and molecular evidence of drug resistance.
2001 Nov 1
Antiviral agents active against human herpesviruses HHV-6, HHV-7 and HHV-8.
2001 Nov-Dec
Multiple herpes simplex virus infections with various resistance patterns in a matched unrelated donor transplant recipient.
2001 Oct
Cidofovir for KS lesions.
2001 Oct
Progressive multifocal leukoencephalopathy in a child with hyperimmunoglobulin E recurrent infection syndrome and review of the literature.
2001 Oct
Cytomegalovirus infection: the point in 2001.
2001 Oct
[Prospects for therapy and prevention of adenovirus keratoconjunctivitis].
2001 Oct
Anti-CD20 monoclonal antibody (Rituximab) and Cidofovir as successful treatment of an EBV-associated lymphoma with CNS involvement.
2001 Oct
Topical treatment of acute adenoviral keratoconjunctivitis with 0.2% cidofovir and 1% cyclosporine: a controlled clinical pilot study.
2001 Oct
A novel nonnucleoside inhibitor specifically targets cytomegalovirus DNA maturation via the UL89 and UL56 gene products.
2001 Oct
Effects of cidofovir on the pathogenesis of a lethal vaccinia virus respiratory infection in mice.
2001 Oct
Bioterrorism. Blocking smallpox: a second defense.
2001 Oct 19
Efficacy of cidofovir on human herpesvirus 8 viraemia and Kaposi's sarcoma progression in two patients with AIDS.
2001 Oct 19
Treatment of a bowenoid papulosis of the penis with local applications of cidofovir in a patient with acquired immunodeficiency syndrome.
2001 Oct 22
Infection due to acyclovir resistant herpes simplex virus in patients undergoing allogeneic hematopoietic stem cell transplantation.
2001 Sep
Strategies for management of cytomegalovirus (CMV) infection after allogeneic bone marrow transplantation: the "doubling of baseline CMV pp65 antigenemia" and the "cidofovir as rescue treatment approaches.
2001 Sep 1
Cidofovir for cytomegalovirus-preemptive therapy in stem cell transplant recipients.
2001 Sep 1
Combined surgical-medical treatment of genital warts in HIV positive patients.
2001 Sep-Oct
Cidofovir-induced end-stage renal failure.
2002 Jan
Patents

Sample Use Guides

Induction Treatment The recommended induction dose of VISTIDE (cidofovir injection) for patients with a serum creatinine of ≤1.5 mg/dL, a calculated creatinine clearance >55 mL/min, and a urine protein <100 mg/dL (equivalent to <2+ proteinuria) is 5 mg/kg body weight (given as an intravenous infusion at a constant rate over 1 hr) administered once weekly for two consecutive weeks. Maintenance Treatment The recommended maintenance dose of VISTIDE is 5 mg/kg body weight (given as an intravenous infusion at a constant rate over 1 hr), administered once every 2 weeks.
Route of Administration: Intravenous
Cidofovir is active in vitro against a variety of laboratory and clinical isolates of cytomegalovirus with IC50 values of 0.5-2.8 uM (WT isolates)
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:16:21 UTC 2021
Edited
by admin
on Sat Jun 26 01:16:21 UTC 2021
Record UNII
768M1V522C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIDOFOVIR ANHYDROUS
Common Name English
CIDOFOVIR [INN]
Common Name English
ANHYDROUS CIDOFOVIR
Common Name English
PHOSPHONIC ACID, ((2-(4-AMINO-2-OXO-1(2H)-PYRIMIDINYL)-1-(HYDROXYMETHYL)ETHOXY)METHYL)-, (S)-
Common Name English
1-((S)-3-HYDROXY-2-(PHOSPHONOMETHOXY)PROPYL)CYTOSINE
Systematic Name English
HPMPC
Common Name English
CIDOFOVIR [HSDB]
Common Name English
(((S)-2-(4-AMINO-2-OXO-1(2H)-PYRIMIDINYL)-1-(HYDROXYMETHYL)ETHOXY)METHYL)PHOSPHONIC ACID
Systematic Name English
CIDOFOVIR [MI]
Common Name English
CIDOFOVIR [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AB12
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
NDF-RT N0000175459
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
NCI_THESAURUS C29575
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
NDF-RT N0000020060
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
NDF-RT N0000175459
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
NDF-RT N0000175459
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
NCI_THESAURUS C281
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
EMA ASSESSMENT REPORTS VISTIDE (WITHDRAWN: CYTOMEGALOVIRUS RETINITIS)
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
NDF-RT N0000175461
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
Code System Code Type Description
EVMPD
SUB25415
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
PRIMARY
EVMPD
SUB06257MIG
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
PRIMARY
EPA CompTox
113852-37-2
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
PRIMARY
FDA UNII
768M1V522C
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
PRIMARY
DRUG BANK
DB00369
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
PRIMARY
MERCK INDEX
M3541
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
PRIMARY Merck Index
CAS
113852-37-2
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
PRIMARY
PUBCHEM
60613
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
PRIMARY
RXCUI
1546007
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C77925
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
PRIMARY
INN
7314
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
PRIMARY
HSDB
7115
Created by admin on Sat Jun 26 01:16:21 UTC 2021 , Edited by admin on Sat Jun 26 01:16:21 UTC 2021
PRIMARY
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SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
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TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
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PRODRUG -> METABOLITE ACTIVE
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ACTIVE MOIETY